Discover the best way to let go of a teetering friendship, marriage or family tie

We all have those people in our lives who subtly, or not so subtly, can make us feel bad about ourselves. But for some reason, whether it's shared history or family ties, we still care about them enough to keep the relationship going. The question is: When is enough enough?

Parting ways with someone you care about—a relative, a friend or a spouse—is never easy, whether the relationship has become destructive or has simply soured over time. Women especially tend to hold on long past the expiration date because it's just too painful to let go. "We stick with a bad relationship out of sheer guilt, which makes it hard for us to pull the plug," says Andrea Bonior, PhD, professor of psychology at Georgetown University and author of The Friendship Fix. "Letting go means putting your needs ahead of someone else's, and women aren't always comfortable with that."

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But if you can find a way to do it, you'll gain much more than you'll lose. "It's like lifting a weight from your shoulders," says Dr. Bonior. "You'll be free of the burden and stress of being taken for granted and giving more than you receive." You'll also rid yourself of someone else's judgment, negativity and unrealistic expectations. Here's how to let go of bad relationships to make room for the good ones.

As difficult as it is to let go of someone, it can be even more painful when you're the dumpee. "No relationship is perfect, so if you said or did something that caused the rift, apologies are in order," says Irene S. Levine, PhD, author of Best Friends Forever: Surviving a Breakup with Your Best Friend. "Do it sooner rather than later, but not while the other person is still upset. And also send a gift or flowers."

However, if after some soul-searching you can't come up with anything you did to alienate the other person, realize that the issue may lie with her, not you. There might be something going on in her life that has impacted your relationship. "Maybe she was depressed or having a family crisis that has nothing to do with you," says Dr. Bonior. "Some people withdraw when they're dealing with personal problems."

Either way, being ditched can haunt you forever, so Dr. Bonior suggests sifting through the rubble to gain some clarity, get over the hurt and find the positives. How? After taking time to be sad and angry, ask yourself the following questions:

Did I get something from the relationship while it was going on?

What did I learn from the breakup of this relationship?

Will I always have some positive memories of this friendship even though it ended badly?

If I'm being honest, am I actually happy that the friendship has ended?

"You can try to win the person back by asking to meet and talk things out," says Dr. Levine, "but if your former friend doesn't respond, then you're the one who'll need to let it go."